#2: He fought Kofi Kingston

WWE Champion Kofi Kingston has had an interesting career to say the least. Debuting on ECW in 2008, Kingston was moved to RAW not long after, where he won the Intercontinental Title. Capturing the United States, WWE Tag, SmackDown Tag, and eventually the WWE Championship, Kingston has enjoyed a truly Hall of Fame worthy career, but did once have a scrap with the Boss.
In Chris Jericho's book The Best In The World: At What I Have No Idea, Y2J tells a story where after a few drinks on a flight with Kingston and Jericho himself, McMahon told Kofi "Maybe you'll get over one of these days." Kofi was going to let it slide, but Jericho told him to challenge Vince to earn his respect.
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After some back and forth tough guy talk, Vince shot in on Kofi with a double leg takedown. The two scuffled in the airplane aisle before McMahon had a good laugh and left the plane. Sure enough, Kofi would get over with the crowd and in 2019 has been one of the company's most popular stars.